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Gambol's gang was at a turf-war with the Italian mob, led by Sal Maroni, and the Russian mob, led by The Chechen. Since the arrival of Batman, Gambol had made a truce with Maroni and the Chechen and formed an Alliance with the other crime organizations as Batman had become a threat.

He acquired an immediate hatred of the Joker, who arrived unannounced to a business meeting between the mob and repeatedly insulted him. Gambol was also displeased with the fact that the Joker stole money from the mob's bank. The Joker also managed to slam one of Gambol's guard's head into a pencil, killing him instantly.

After placing a bounty on him, Gambol was tricked by a trio of bounty hunters who made it seem like they brought him the Joker dead. The Joker revealed himself alive after stabbing two of Gambol's men with knives, pressed a knife in Gambol's mouth, and told him an ambiguous story of how he got his scars. The Joker then instantly killed Gambol with his knife.

Gambol's empire was destroyed for good after the Joker made his last surviving men fight to the death with half of a broken pool stick.